


Free to Be Destiel

by CaptainShade



Series: Supernatural Kink Bingo 2019 [4]
Category: Supernatural
Genre: Awkward First Times, Cas doesn't know it's premature, Episode: s05e03 Free to Be You and Me, First Kiss, Frottage, M/M, Premature Ejaculation, Sort Of, holy oil as lube
Language: English
Status: Completed
Published: 2019-07-15
Updated: 2019-07-15
Packaged: 2020-06-28 11:38:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 901
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19811521
Author URL: https://archiveofourown.org/users/CaptainShade/pseuds/CaptainShade
Summary: Free to Be You and Me tag/coda/alteration, whatever. Instead of taking Cas to a brothel to lose his virginity, they get it on in the abandoned house the night before summoning Raphael. Cas is tense. Dean is left hanging.Unbetaed, all mistakes are my own (don't hesitate to point them out in the comments).





	Free to Be Destiel

**Author's Note:**

> Free to Be You and Me tag/coda/alteration, whatever. Instead of taking Cas to a brothel to lose his virginity, they get it on in the abandoned house the night before summoning Raphael. Cas is tense. Dean is left hanging.  
> Unbetaed, all mistakes are my own (don't hesitate to point them out in the comments).

“There are two things I know for sure,” Dean Winchester said, toeing off his boots and kicking them under the table. “Bert and Ernie are gay,” his overshirt landed on the back of the chair, “and you are not gonna die a virgin.” 

“Dean--”

“Before I assume shit I really shouldn’t, I’m gonna lay it out. I’ve been eyeing your ass since the barn in Illinois, and I’m pretty sure you’ve been looking at mine too. If you don’t wanna spend your last night on Earth getting down and dirty, you just say the word. But from the looks of  _ that _ ,” he nodded at the growing bulge in Cas’s trousers, “you wouldn’t mind. Am I wrong?”

The angel shifted in his seat. Opened and closed his mouth a few times, staring at Dean’s lips and torso where his Henley had ridden up. Swallowed with a dry click. 

“No,” he finally replied. “You are not incorrect.” 

“Great!” His grin was sharp, but not predatory. “I’m not doing this on the floor, so go lay down on the bed, and I’ll take care of you.” He pulled his shirt over his head, muffling his voice, but Castiel dutifully sat on the bed, hands rigid on his lap, somehow managing both nervousness and lust on his face at the same time. 

Dean looked up from unbuttoning his jeans. “Cas. Buddy--uh, baby. You gotta relax. Just because I’m not getting inside you doesn’t mean you should be tense.” He shoved his pants off and rummaged around in his duffel for lube. “Shit. The one night I need the KY, I leave it in the car. Is somebody gonna strike me down if I use some of the holy oil for this? Two men goin’ at it, s’that offend anybody up there?”

Cas squinted at him. “Heaven doesn’t concern itself with the sexes of intimate partners.” Was it a trick of the light, or did Cas’s pupils blow up when he said ‘intimate’? 

Dean felt himself twitch in his boxers.

It was past time to get this show on the road. 

He set the jug of oil next to the bed as gently as he could with adrenaline-fueled hands and shoved Cas onto the bed, straddling his hips before the angel could tense up again. Of course, it was hard to tell when he was tensed and when he wasn’t, since his body was abnormally firm. Either an angel thing, or Jimmy was ripped.

“Dude, you’re still fully dressed. I’m all for a little kinky dress-up, but I’m not riding a guy in, like, four layers. Help me out here.” Together they managed to get the trench coat off without getting completely off the bed, and the suit jacket got flung somewhere by the chairs. It looked nice enough that Jimmy’d probably be a little ticked, but--

Oh, shit. Jimmy.

“Wait, wait. What does Jimmy think about all this? I don’t want somebody who doesn’t want to hitching a ride.”

“When Father brought me back, James Novak wasn’t here. You don’t need to worry about him anymore.”

“Glad we got that out of the way.” 

Castiel had relaxed somewhat, probably distracted by the unplanned conversation, but as soon as Dean reached for his waistband, he was a board again. 

“Cas, sex is supposed to feel good, not stressful. I know this is your first time, but I know what I’m doing. Just--calm down, okay? Feel, don’t think.”

It took a few moments of soulful staring, but he finally relaxed into the threadbare mattress, and Dean watched his expression as he unbuttoned his shirt and pushed it off his shoulders. 

Jimbo was a lot more ripped than Dean would have guessed. What was he, a body-building choir-boy? Well. That wouldn’t go unappreciated. 

Dean let his hands roam over Cas’s torso when he bent to kiss him. Softly, because the angel was new at this. Definitely the only reason. 

Cas’s hands found his hips and pulled him more firmly into the cradle of his groin, and they both gasped. Cas broke the kiss and stared at Dean with wide eyes, rocking Dean against him a second time. Dean smirked at the shocked moan falling from Cas’s lips. 

“See? Told you it’s supposed to feel good--Woah!”

Castiel flipped them and started grinding before Dean knew what was happening, chasing his very first orgasm in ever. Cas hiked Dean’s legs up around his waist and caught the head of his dick behind Dean’s balls, a shudder rushing through him at the feeling. The angel ducked his head and attacked Dean’s mouth with his own, biting and licking in a very uncoordinated way and grinding his dick behind his balls a few more times before spilling sticky and hot in his boxers. Dean groaned, half frustration and half arousal, rubbing his cock against Cas’s abs and chasing his own orgasm. 

It wasn’t going to happen like this. 

“Cas, buddy, can you give me some--” he made a couple unsubtle jerking motions with the hand that wasn’t trapped between their bodies. 

Apparently, it was too subtle for the newly de-flowered virgin, because he just made a confused, lazy noise and didn’t move. 

“Come on man, don’t leave me hangin’.”

Again, no movement. 

Dean sighed and tried to pull his hand out from between their chests so he could finish himself off. 

It was going to be a long night. 


End file.
